Reaktion #65893

Reaktionsgleichung

4-methylphenyl boronic acid

sodium carbonate

water

Compound C

5-(2-bromophenyl)-1-(4-nitrophenyl)-1H-tetrazole

→

5-(4'-methylbiphenyl-2-yl)-1-(4-nitrophenyl)-1H-tetrazole

Ausbeute 95.1%

Lösungsmittel

toluene

methanol

Toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeto give a clear solution
2. 2
   Temperaturthe mixture heated
3. 3
   Temperaturat reflux for 3 hours
4. 4
   Filtrationthe warm mixture was filtered through diatomaceous earth
5. 5
   SonstigeThe organic phase was separated
6. 6
   Extraktionthe aqueous phase extracted with toluene (40 ml)
7. 7
   SonstigeThe combined organic phases were evaporated
8. 8
   Sonstigeto give a solid which
9. 9
   Sonstigewas recrystallised from toluene/petroleum ether (100°-120° C.) (1:1 v/v)

Vorschrift

A mixture of 4-methylphenyl boronic acid (9.7 g; 71 mmol), sodium carbonate (16.7 g; 158 mmol), water (100 ml), methanol (50 ml) and toluene (50 ml) was heated to 60° C. to give a clear solution. Compound C (20.0 g; 55 mmol) was then added, followed by tetrakis(triphenylphosphine)palladium (0.3 g; 0.25 mmol) and the mixture heated at reflux for 3 hours. Toluene (30 ml) was added and the warm mixture was filtered through diatomaceous earth. The organic phase was separated and the aqueous phase extracted with toluene (40 ml). The combined organic phases were evaporated to give a solid which was recrystallised from toluene/petroleum ether (100°-120° C.) (1:1 v/v) to give 5-(4'-methylbiphenyl-2-yl)-1-(4-nitrophenyl)-1H-tetrazole (D) (18.7 g; 90% yield), m.p. 164°-166° C.; NMR (CDCl3): 2.3(3H, s), 6.45(2H, d), 6.85(4H, m), 7.38(1H, d), 7.65(2H, m), 7.85(1H, d), 8.0(2H, d).

Quelle